EA008191B1 - Сшитые блок-сополимеры стирола и способ их получения - Google Patents
Сшитые блок-сополимеры стирола и способ их получения Download PDFInfo
- Publication number
- EA008191B1 EA008191B1 EA200500161A EA200500161A EA008191B1 EA 008191 B1 EA008191 B1 EA 008191B1 EA 200500161 A EA200500161 A EA 200500161A EA 200500161 A EA200500161 A EA 200500161A EA 008191 B1 EA008191 B1 EA 008191B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- styrene
- polymer
- block copolymer
- bitumen
- living
- Prior art date
Links
- 229920006132 styrene block copolymer Polymers 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 54
- 239000010426 asphalt Substances 0.000 claims abstract description 44
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- -1 alkyl compound Chemical class 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 239000004568 cement Substances 0.000 claims abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 57
- 229920001400 block copolymer Polymers 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001993 dienes Chemical group 0.000 claims description 14
- 239000003431 cross linking reagent Substances 0.000 claims description 12
- 150000005690 diesters Chemical class 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 239000011414 polymer cement Substances 0.000 claims description 10
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 3
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims 1
- 229920002857 polybutadiene Polymers 0.000 claims 1
- 229920001195 polyisoprene Polymers 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 3
- 230000004048 modification Effects 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract description 2
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 22
- 238000004132 cross linking Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000011269 tar Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- ABIAVOPWHAWUGT-UHFFFAOYSA-N zinc;2-methanidylpropane Chemical compound [Zn+2].CC(C)[CH2-].CC(C)[CH2-] ABIAVOPWHAWUGT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/044—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a coupling agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
- C08L53/025—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes modified
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Civil Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39513902P | 2002-07-11 | 2002-07-11 | |
PCT/US2003/021814 WO2004007581A1 (en) | 2002-07-11 | 2003-07-11 | Coupled styrenic block copolymers and process for preparing same |
Publications (2)
Publication Number | Publication Date |
---|---|
EA200500161A1 EA200500161A1 (ru) | 2005-08-25 |
EA008191B1 true EA008191B1 (ru) | 2007-04-27 |
Family
ID=30115821
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA200500161A EA008191B1 (ru) | 2002-07-11 | 2003-07-11 | Сшитые блок-сополимеры стирола и способ их получения |
Country Status (12)
Country | Link |
---|---|
US (1) | US7009000B2 (ko) |
EP (1) | EP1532185B1 (ko) |
JP (1) | JP4368303B2 (ko) |
KR (1) | KR100626442B1 (ko) |
CN (1) | CN1302036C (ko) |
AT (1) | ATE397632T1 (ko) |
AU (1) | AU2003249169A1 (ko) |
BR (1) | BR0312603B1 (ko) |
DE (1) | DE60321467D1 (ko) |
EA (1) | EA008191B1 (ko) |
ES (1) | ES2307979T3 (ko) |
WO (1) | WO2004007581A1 (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9328235B2 (en) | 2008-07-21 | 2016-05-03 | Lg Chem, Ltd. | Asphalt modifier composition and asphalt composition comprising the same |
RU2703175C2 (ru) * | 2010-05-31 | 2019-10-15 | Бриджстоун Корпорейшн | Содержащий гидроксильные группы метилстирол и полимеры на его основе |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7125940B2 (en) | 2002-12-31 | 2006-10-24 | Kraton Polymers U.S. Llc | Conjugated diene polymers and copolymer blocks and process for preparing same |
US8151281B2 (en) | 2004-01-09 | 2012-04-03 | International Business Machines Corporation | Method and system of mapping at least one web service to at least one OSGi service |
US7465768B2 (en) * | 2004-06-18 | 2008-12-16 | Bridgestone Corporation | Method to reduce coupling during termination with functional end-groups |
US7449518B2 (en) * | 2006-03-24 | 2008-11-11 | Kraton Polymers U.S. Llc | High temperature block copolymers and process for making same |
KR100923535B1 (ko) * | 2007-11-21 | 2009-10-27 | 금호석유화학 주식회사 | 테이퍼드된 블록 공중합체를 함유한 개질 아스팔트 조성물 |
US8883927B2 (en) * | 2007-11-28 | 2014-11-11 | Dynasol Elastómeros, S.A. De C.V. | Radial multi-block copolymers |
CN101903455B (zh) | 2007-12-21 | 2013-01-16 | 科腾聚合物美国有限责任公司 | 软质弹性体膜 |
US20100316820A1 (en) * | 2009-06-16 | 2010-12-16 | Rainer Kolb | Composite Materials Comprising Propylene-Based Polymer Blend Coatings |
WO2011053406A1 (en) * | 2009-10-29 | 2011-05-05 | Exxonmobil Chemical Patents Inc. | Pressure-sensitive hot melt adhesive compositions |
US9023950B2 (en) | 2010-04-21 | 2015-05-05 | Nippon Soda Co., Ltd. | Star polymer and method of producing same |
KR101411159B1 (ko) * | 2010-08-03 | 2014-06-23 | 주식회사 엘지화학 | 아스팔트의 열 안정성 개선을 위한 삼중 가지형 비닐 방향족 탄화수소-공액디엔 블록 공중합체 조성물, 이의 제조방법, 및 이를 포함하는 아스팔트 조성물 |
WO2015054457A1 (en) * | 2013-10-11 | 2015-04-16 | Kraton Polymers U.S. Llc | An olefinically unsaturated radial styrenic block copolymer and an improved vulcanizer-free latex |
US10472514B2 (en) * | 2014-01-23 | 2019-11-12 | Asahi Kasei Kabushiki Kaisha | Block copolymer composition and adhesive composition |
KR101688504B1 (ko) * | 2014-07-15 | 2016-12-22 | 금호석유화학 주식회사 | 개질 아스팔트용 첨가제 조성물, 이를 포함하는 개질 아스팔트 조성물, 및 그 제조 방법 |
US9428628B2 (en) | 2014-08-20 | 2016-08-30 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
US10385156B2 (en) | 2016-06-30 | 2019-08-20 | Kraton Polymers U.S. Llc | Performance high vinyl block copolymer compositions and uses thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5272214A (en) * | 1986-12-01 | 1993-12-21 | Enichem Elastomeri S.P.A. | Radial and branched block copolymers, compositions which contain them, their preparation and their use in bituminous compositions |
US5552493A (en) * | 1995-05-30 | 1996-09-03 | Shell Oil Company | Method for producing asymmetric radial polymers |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3631006A (en) | 1965-09-01 | 1971-12-28 | Cities Service Co | Process for the anionic polymerization of unsaturated hydrocarbon monomers |
US4518753A (en) | 1982-04-26 | 1985-05-21 | National Research Development Corporation | Anionic polymerization of conjugated dienes in the presence of hindered triaryl boron or aluminum derivatives |
US4530984A (en) | 1982-07-01 | 1985-07-23 | The Firestone Tire & Rubber Company | Process for production of polymers having increased 1,2-microstructure |
US4476240A (en) | 1982-07-01 | 1984-10-09 | The Firestone Tire & Rubber Company | Catalyst system containing an anionic initiator based on lithium and phosphine oxide modifier |
US4473661A (en) | 1982-07-01 | 1984-09-25 | The Firestone Tire & Rubber Company | Polymerization catalyst system containing organolithium, dialkyl magnesium and/or trialkyl aluminum, and a phosphine oxide |
US4429091A (en) | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators |
US4429090A (en) | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Catalyst containing oligomeric oxolanyl alkane modifiers and process for the production of polymers having increased 1,2-microstructure |
US4480075A (en) | 1983-06-24 | 1984-10-30 | Shell Oil Company | Block copolymers of Ziegler-Natta polymerized and anionically polymerized monomers |
US4591624A (en) | 1984-07-02 | 1986-05-27 | The Firestone Tire & Rubber Company | Catalyst system and process for polymerizing conjugated dienes |
US4520123A (en) | 1984-07-02 | 1985-05-28 | The Firestone Tire & Rubber Company | Catalyst system and process for polymerizing conjugated dienes |
US5202499A (en) | 1988-05-31 | 1993-04-13 | Gencorp Inc. | Liquid telechelic polymers having high 1,4-diene structure |
US5063190A (en) | 1988-05-31 | 1991-11-05 | Gencorp Inc. | Anionic initiator system for polymerizing monomers |
US5216181A (en) | 1988-05-31 | 1993-06-01 | Gencorp Inc. | Liquid telechelic polymers having high 1,4-diene structure |
US4889900A (en) | 1989-06-12 | 1989-12-26 | Shell Oil Company | Preparation of alkyl methacrylate monomers for anionic polymerization |
GB9002804D0 (en) | 1990-02-08 | 1990-04-04 | Secr Defence | Anionic polymerisation |
US5397851A (en) | 1993-11-09 | 1995-03-14 | Polysar Rubber Corporation | Process for cis-1,4-polybutadiene production with reduced gel formation |
US5376745A (en) | 1993-12-01 | 1994-12-27 | Shell Oil Company | Low viscosity terminally functionalized isoprene polymers |
FR2714384B1 (fr) * | 1993-12-29 | 1996-02-02 | Atochem Elf Sa | Copolymère bloc étoile d'un monomère vinylaromatique et d'un diène conjugué, son procédé d'obtention, et les compositions comprenant ledit copolymère et du polystyrène cristal. |
US5416168A (en) | 1994-03-31 | 1995-05-16 | Shell Oil Company | Protected functional initiators for making terminally functionalized polymers |
US5420203A (en) * | 1994-05-17 | 1995-05-30 | Shell Oil Company | Process for producing high diblock content block copolymer compositions |
US5412045A (en) | 1994-09-16 | 1995-05-02 | Polysar Rubber Corporation | Preparation of high cis-1,4-polybutadiene with reduced gel |
US5610227A (en) | 1995-06-07 | 1997-03-11 | Bridgestone/Firestone, Inc. | Lithium amino magnesiate polymerization initiators and elastomers having reduced hysteresis |
US6429273B1 (en) | 1996-03-14 | 2002-08-06 | Asahi Kasei Kabushiki Kaisha | Process for the preparation of vinylic polymers, polymerization initiator for vinylic monomers, and styrene resin composition |
KR100487452B1 (ko) | 1996-08-19 | 2005-05-09 | 바스프 악티엔게젤샤프트 | 음이온 중합 방법 |
WO1998007766A1 (de) | 1996-08-19 | 1998-02-26 | Basf Aktiengesellschaft | Verfahren zur herstellung von dienpolymerisatlösungen in vinylaromatischen monomeren |
US5665827A (en) | 1996-11-07 | 1997-09-09 | Bridgestone Corporation | Synthesis of multiblock polymers using group IIA and IIB metal cyclic organometallic initiators |
US5700888A (en) | 1996-11-07 | 1997-12-23 | Bridgestone Corporation | Synthesis of macrocyclic polymers having low hysteresis compounded properties |
US5677399A (en) | 1996-11-07 | 1997-10-14 | Bridgestone Corporation | Synthesis of macrocyclic polymers with group IIA and IIB metal cyclic organometallic initiators |
DE19648565A1 (de) | 1996-11-23 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung von Polyalkyl(meth)acrylaten |
US6462143B1 (en) | 1998-02-03 | 2002-10-08 | Kraton Polymers Us Llc | Gel-free process for making functionalized anionically polymerized polymers |
ES2211047T3 (es) * | 1998-02-07 | 2004-07-01 | Basf Aktiengesellschaft | Procedimiento para la obtencion de masas de moldeo termoplasticas, modificadas a la resiliencia. |
US6242537B1 (en) | 1998-03-30 | 2001-06-05 | Shell Oil Company | Gel-free process for making hydrogenated functionalized anionically polymerized polymers |
TW442498B (en) | 1998-05-18 | 2001-06-23 | Shell Internattonale Res Mij B | Process for making anionic polymeric di-and polyfunctional polymers using protected functional initiators, and functionalised polymer producted thereby |
US6242538B1 (en) | 1998-06-04 | 2001-06-05 | Shell Oil Company | Process for making hydrogenated gel-free functionalized anionically polymerized polymers |
US6455651B1 (en) | 1999-04-23 | 2002-09-24 | Kraton Polymers U.S. Llc | Uniform initiation of anionic polymerization using organo-substituted alkali metal initiators |
US6391981B1 (en) | 1999-04-23 | 2002-05-21 | Kraton Polymers Us Llc | Increased throughput in the manufacture of anionic polymers by reduction in polymer cement viscosity through the addition of metal alkyls |
US20030114611A1 (en) | 2001-10-24 | 2003-06-19 | Fmc Corporation | Functionalized alkyllithium formulations with improved thermal stability and processes for making the same |
US20030114592A1 (en) | 2001-10-24 | 2003-06-19 | Fmc Corporation | Processes for improving stability of living polymer chain ends |
-
2003
- 2003-07-11 JP JP2004521737A patent/JP4368303B2/ja not_active Expired - Fee Related
- 2003-07-11 AU AU2003249169A patent/AU2003249169A1/en not_active Abandoned
- 2003-07-11 AT AT03764565T patent/ATE397632T1/de not_active IP Right Cessation
- 2003-07-11 CN CNB038197987A patent/CN1302036C/zh not_active Expired - Fee Related
- 2003-07-11 KR KR1020057000555A patent/KR100626442B1/ko active IP Right Grant
- 2003-07-11 WO PCT/US2003/021814 patent/WO2004007581A1/en active Application Filing
- 2003-07-11 EA EA200500161A patent/EA008191B1/ru not_active IP Right Cessation
- 2003-07-11 BR BRPI0312603-0A patent/BR0312603B1/pt not_active IP Right Cessation
- 2003-07-11 DE DE60321467T patent/DE60321467D1/de not_active Expired - Lifetime
- 2003-07-11 US US10/618,394 patent/US7009000B2/en not_active Expired - Lifetime
- 2003-07-11 EP EP03764565A patent/EP1532185B1/en not_active Expired - Lifetime
- 2003-07-11 ES ES03764565T patent/ES2307979T3/es not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5272214A (en) * | 1986-12-01 | 1993-12-21 | Enichem Elastomeri S.P.A. | Radial and branched block copolymers, compositions which contain them, their preparation and their use in bituminous compositions |
US5552493A (en) * | 1995-05-30 | 1996-09-03 | Shell Oil Company | Method for producing asymmetric radial polymers |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9328235B2 (en) | 2008-07-21 | 2016-05-03 | Lg Chem, Ltd. | Asphalt modifier composition and asphalt composition comprising the same |
RU2703175C2 (ru) * | 2010-05-31 | 2019-10-15 | Бриджстоун Корпорейшн | Содержащий гидроксильные группы метилстирол и полимеры на его основе |
Also Published As
Publication number | Publication date |
---|---|
BR0312603B1 (pt) | 2012-12-11 |
CN1302036C (zh) | 2007-02-28 |
EA200500161A1 (ru) | 2005-08-25 |
DE60321467D1 (de) | 2008-07-17 |
BR0312603A (pt) | 2005-05-31 |
JP4368303B2 (ja) | 2009-11-18 |
WO2004007581A1 (en) | 2004-01-22 |
JP2005533151A (ja) | 2005-11-04 |
CN1675272A (zh) | 2005-09-28 |
KR20050021458A (ko) | 2005-03-07 |
AU2003249169A1 (en) | 2004-02-02 |
US20040054090A1 (en) | 2004-03-18 |
ES2307979T3 (es) | 2008-12-01 |
ATE397632T1 (de) | 2008-06-15 |
KR100626442B1 (ko) | 2006-09-20 |
US7009000B2 (en) | 2006-03-07 |
EP1532185A1 (en) | 2005-05-25 |
EP1532185B1 (en) | 2008-06-04 |
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